EVENTS & VENUE

Our Vision Comes with Breathtaking Views.

Whether attending one of our signature annual events or hosting your own at our unique reception space in the Charlestown Navy Yard, you are providing critical support for the Courageous mission.
Explore our Calendar
For a uniquely Boston event or outing, look no further than Pier 4. Our experienced team and preferred vendors will partner with you to make every detail unforgettable.

Annual Courageous Events

The Gala

Each fall, we share and celebrate the impact of Courageous Sailing programs with an elegant cocktail party. We invite you to join us as a guest, sponsor, or volunteer.
Learn More

Flip Flop Regatta

One of New England’s largest regattas of the season, Flip Flop is a pursuit-style race held in August and open to all monohull sailing vessels 21 feet LOA and larger. Let the race begin!
Learn More

Corporate Challenge

A fixture of the New England college-sailing circuit, the Richard B. Ross College Bowl was established in 2004 and generates crucial funding for Courageous’ youth sailing programs.
Learn More

More Ways to Get Involved

College Bowl Rhodes 19 Racing

Richard B. Ross College Bowl

A fixture of the New England college-sailing circuit, the Richard B. Ross College Bowl was established in 2004 and generates crucial funding for Courageous’ youth sailing programs.
Learn More
Image

Private Sails

Take the sails or just take it easy. Our private sails provide access to one-on-one instruction in a lesson format, or the peace of a private harbor cruise.
Learn More
Image

Become a Volunteer

As a non-profit organization, Courageous relies on the support of volunteers to run things smoothly. Get in touch if you're willing to lend a hand.

Learn More

    2024 Courageous Open House

    11 AM to 2 PM on Saturday April 22 and Sunday April 23.
    Everyone’s invited! Our annual open house is your chance to check out our space at Pier 4, join us for a free 20-minute sail, and learn all about Courageous memberships and programming. Enjoy community, light refreshments, and fabulous views of the city.
    Reserve a Time